Citric Acid → 4-(5-Bromopentyl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-5-one

HRID 466961

Reaktionsgleichung

Reaktionsgleichung von HRID 466961
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[NH:4][CH2:3][CH2:2]1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:4]1[C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:1][CH2:2][CH2:3]1

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 3406292,3,4,5-Tetrahydro-1,4-benzoxazepin-5-one

Produkt 1

HCID 198130564-(5-Bromopentyl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-5-oneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 20 ml of dimethylformamide (DMF) was dissolved 100 mg of 2,3,4,5-tetrahydro-1,4-benzoxazepin-5-one, and the solution then ice-cooled. Then, to the resulting solution were added 0.251 ml (3 equivalents) of 1,5-dibromopentane and 29.4 mg (1.2 equivalent) of a 60% sodium hydride oil dispersion, and the mixture was stirred for one hour with ice-cooling. The reaction solution was poured into a citric acid aqueous solution and extracted with ethyl acetate, and the ethyl acetate phase was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was then concentrated and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (8:2)) to give 124 mg (yield: 65.0%) of the title compound.

Aufarbeitung

  1. temperaturethe solution then ice-cooled
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washthe ethyl acetate phase was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was then concentrated
  8. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (8:2))

Quellen und Nachweise

ORD-Eintrag
ord-5a307d9441d2491899e5958bbc821fa0
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158947

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